AU2004299258A1 - 6-(2-halophenyl)-triazolopyrimidines, method for their production and their use for combating pathogenic fungi, in addition to agents containing said substances - Google Patents

Description

IN THE MATTER OF an Australian Application corresponding to PCT Application PCT/EP2004/014328 RWS Group Ltd, of Europa House, Marsham Way, Gerrards Cross, Buckinghamshire, England, hereby solemnly and sincerely declares that, to the best of its knowledge and belief, the following document, prepared by one of its translators competent in the art and conversant with the English and German languages, is a true and correct translation of the PCT Application filed under No. PCT/EP2004/014328. Date: 18 April 2006 S. ANTHONY Director For and on behalf of RWS Group Ltd 1 6-(2-Halophenyl)-triazolopyrimidines, method for their production and their use for combating pathogenic fungi, in addition to agents comprising said substances The present invention relates to substituted triazolopyrimidines of the formula I 5 L 1 2 3 N N'-N L 2 N NLX N -N/' Hal in which the substituents are as defined below: 10 R 1 , R 2 independently of one another are hydrogen, C 1

-C

8 -alkyl, C 1

-C

8 -haloalkyl,

C

3

-C

8 -cycloalkyl, C 3

-C

8 -halocycloalkyl, C 2

-C

8 -alkenyl, C 2

-C

8 -haloalkenyl, C 3

-C

6 cycloalkenyl, C 3

-C

6 -halocycloalkenyl, C 2

-C

8 -alkynyl, C 2

-C

8 -haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of 15 O, N and S,

R

1 and R 2 together with the nitrogen atom to which they are attached may also form a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain one to three further heteroatoms from the group consisting of O, 20 N and S as ring member and/or may carry one or more substituents from the group consisting of halogen, Cl-C 6 -alkyl, Cl-C 6 -haloalkyl, C 2

-C

6 -alkenyl, C 2

-C

6 haloalkenyl, Cl-C 6 -alkoxy, C 1

-C

6 -haloalkoxy, C 3

-C

6 -alkenyloxy, C 3

-C

6 haloalkenyloxy, C0 1

-C

6 -alkylene and oxy-C0 1

-C

3 -alkyleneoxy; 25 R' and/or R 2 may carry one to four identical or different groups Ra:

R

a is halogen, cyano, nitro, hydroxyl, C 1

-C

6 -alkyl, Cl-C 6 -haloalkyl, Cs-C6 alkylcarbonyl, C 3

-C

6 -cycloalkyl, C 1

-C

6 -alkoxy, C 1 l-C 6 -haloalkoxy, Cl-C6 alkoxycarbonyl, Cl-C 6 -alkylthio, Cl-C 6 -alkylamino, di-Cl-C 6 -alkylamino, 30 C 2

-C

8 -alkenyl, C 2

-C

8 -haloalkenyl, C 3

-C

8 -Cycloalkenyl, C 2

-C

6 -alkenyloxy,

C

3

-C

6 -haloalkenyloxy, C 2

-C

6 -alkynyl, C 2

-C

6 -haloalkynyl, C 3

-C

6 -alkynyloxy,

C

3

-C

6 -haloalkynyloxy, C 3

-C

6 -cycloalkoxy, C 3

-C

6 -cycloalkenyloxy, Cl-C 3 oxyalkyleneoxy, phenyl, naphthyl, a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four 35 heteroatoms from the group consisting of O, N and S, 2 where these aliphatic, alicyclic or aromatic groups for their part may be partially or fully halogenated or may carry one to three groups Rb: Rb is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, 5 aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothio 10 carbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the abovementioned alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms; and/or one to three of the following radicals: 15 cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl

C

1

-C

6 -alkoxy, aryl-C 1

-C

6 -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members and the 20 hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or substituted by alkyl or haloalkyl groups; Hal is halogen; 25

L

1 , L 2 are hydrogen, cyano, Cl-C 4 -haloalkyl, CI-C 6 -alkoxy, C 3

-C

6 -alkenyloxy or C(=O)A, where at least one group Ll or L 2 is not hydrogen; A is hydrogen, hydroxy, C 1

-C

8 -alkyl, C 1

-C

8 -alkoxy, Cl-C 6 -haloalkoxy, Cj-C 8 30 alkylamino or di-(C-C 8 -alkyl)amino;

L

3 is hydrogen, halogen, cyano, nitro, C 1

-C

4 -haloalkyl, Cl-C 6 -alkoxy,

C

1

-C

6 -alkoxycarbonyl; 35 X is halogen, cyano, C 1

-C

4 -alkyl, C 1

-C

4 -haloalkyl, C 1

-C

4 -alkoxy or Cl-C 2 -haloalkoxy. Moreover, the invention relates to processes and intermediates for preparing these compounds, to compositions comprising them and to their use for controlling phytopathogenic harmful fungi.

3 5-Chloro-6-phenyl-7-aminotriazolopyrimidines are known in a general manner from EP-A 71 792 and EP-A 550 113. 6-Phenyltriazolopyrimidines whose phenyl group may, in the para-position, carry an alkylamide group are proposed in a general manner in 5 WO 03/080615. It is known that these compounds are suitable for controlling harmful fungi. The compounds according to the invention differ from those described in WO 03/080615 by the position of the alkylamide group as a substituent of the 6-phenyl 10 ring. However, the action of the prior-art compounds is in many cases unsatisfactory. It is an object of the present invention to provide compounds having improved activity 15 and/or a broader activity spectrum. We have found that this object is achieved by the compounds defined at the outset. Furthermore, we have found processes and intermediates for their preparation, compositions comprising them and methods for controlling harmful fungi using the 20 compounds I. The compounds according to the invention can be obtained by different routes. Advantageously, they are prepared by reacting 5-aminotriazole of the formula II with appropriately substituted phenylmalonates of the formula Ill in which R is alkyl, 25 preferably C 1

-C

6 -alkyl, in particular methyl or ethyl. L L N-NH

L

3 OH NH RO L2 N'N L 2 N-J- NH 2 ROl N al RO Oa N C IV II RO Hal IIIN -al IV This reaction is usually carried out at temperatures of from 800C to 2500C, preferably 30 from 1200C to 1800C, in the absence of a solvent or in an inert organic solvent in the presence of a base [cf. EP-A 770 615] or in the presence of acetic acid under the conditions known from Adv. Het. Chem. 57 (1993), 81ff. Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, such as toluene, 35 o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and 4 also N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide. The reaction is particularly preferably carried out in the absence of a solvent or in chlorobenzene, xylene, dimethyl sulfoxide or N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned. 5 Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates, and also alkali metal bicarbonates, organometallic compounds, in 10 particular alkali metal alkyls, alkylmagnesium halides and also alkali metal and alkaline earth metal alkoxides and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, triisopropylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular 15 preference is given to tertiary amines such as triisopropylamine, tributylamine, N-methylmorpholine or N-methylpiperidine. The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvents. 20 The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of base and malonate III, based on the triazole. 25 Phenylmalonates of the formula III are advantageously obtained by reacting appropriately substituted bromobenzenes with dialkyl malonates under Cu(I) catalysis [cf. Chemistry Letters (1981), 367-370; EP-A 10 02 788]. The dihydroxytriazolopyrimidines of the formula IV are converted under the conditions 30 known from WO-A 94/20501 into the dihalopyrimidines of the formula V in which Y is a halogen atom, preferably a bromine or a chlorine atom, in particular a chlorine atom. Advantageous halogenating agents [HAL] are chlorinating agents or brominating agents, such as phosphorus oxybromide or phosphorus oxychloride, if appropriate in the presence of a solvent. 35 5 L L3 [HAL] Y IV NN L 2 V S Hal N N Y This reaction is usually carried out at from 00C to 150 0 C, preferably at from 80'C to 1250C [cf. EP-A 770 615]. 5 Dihalopyrimidines of the formula V are reacted further with amines of the formula VI RL V + R2N-H I (X = halogen) VI 10 in which R 1 and R 2 are as defined in formula I, to give compounds of the formula I in which X is halogen. This reaction is advantageously carried out at from 00C to 700C, preferably from 100C to 350C, preferably in the presence of an inert solvent, such as an ether, for example 15 dioxane, diethyl ether or, in particular, tetrahydrofuran, a halogenated hydrocarbon, such as dichloromethane, or an aromatic hydrocarbon, such as, for example, toluene [cf. WO-A 98/46608]. Preference is given to using a base, such as a tertiary amine, for example 20 triethylamine, or an inorganic base, such as potassium carbonate; it is also possible for excess amine of the formula VI to serve as base. Compounds of the formula I in which X is cyano, C 1

-C

6 -alkoxy or C 1

-C

2 -haloalkoxy can advantageously be obtained by reacting compounds I in which X is halogen, preferably 25 chlorine, with compounds M-X' (formula VII). Depending on the meaning of the group X' to be introduced, the compounds VII are inorganic cyanaides, alkoxides or haloalkoxides. The reaction is advantageously carried out in the presence of an inert solvent. The cation M in formula VII is of little importance; for practical reasons, preference is usually given to ammonium, tetraalkylammonium or alkali metal or 30 alkaline earth metal salts. I (X = halogen) + M-X' 1 (X = X')

VII

6 The reaction temperature is usually from 0 to 1200C, preferably from 10 to 400C [cf. J. Heterocycl. Chem. 12 (1975), 861-863]. 5 Suitable solvents include ethers, such as dioxane, diethyl ether and, preferably, tetrahydrofuran, alcohols, such as methanol or ethanol, halogenated hydrocarbons, such as dichloromethane, and aromatic hydrocarbons, such as toluene or acetonitrile. Compounds of the formula I in which X is C 1

-C

4 -alkyl or C 1

-C

4 -haloalkyl can 10 advantageously be obtained by the following synthesis route:

L

1 L

XL

3 OH O L OH + RO L2 N'-N L2 S Hal N Hal SIlia N N X IVa Starting with the ketoesters Ilia, the 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines IVa 15 are obtained. In the formulae lila and IVa, X 1 is C 1

-C

4 -alkyl or C 1

-C

4 -haloalkyl. If the easily obtainable 2-phenylacetoacetates (Ilia where X'=CH 3 ) are used, 5-methyl 7-hydroxy-6-phenyltriazolopyrimidines are obtained [cf. Chem. Pharm. Bull. 9 (1961), 801]. The starting materials lila are advantageously prepared under the conditions described in EP-A 10 02 788. 20 The resulting 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines are reacted with halogenating agents [HAL] under the conditions described further above to give the 7-halotriazolopyrimidines of the formula Va in which Y is a halogen atom. Preference is given to using chlorinating or brominating agents, such as phosphorus oxybromide, 25 phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride. The reaction can be carried out neat or in the presence of a solvent. Customary reaction temperatures are from 0 to 150 0 C or, preferably, from 80 to 125 0 C.

L

1 3 .~Ly N' N L 2 + VI I (X = alkyl) N N X Hal Va 30 7 The reaction of Va with amines VI is carried out under the conditions described further above. Alternatively, compounds of the formula I in which X is C 1

-C

4 -alkyl can also be 5 prepared from compounds I in which X is halogen, in particular chlorine, and malonates of the formula VIII. In the formula VIII, X" is hydrogen or C 1

-C

3 -alkyl and R is C 1

-C

4 alkyl. They are converted into compounds of the formula IX and decarboxylated to give the compounds I [cf. US 5,994,360]. L 1 2 3 X" RN 0 0-N 2 I(X=Hal) + /N'N L OR OR N N Hal VilN N X11 IX 10VIII ROOC COOR IX 10

A/H

+ IX I (X = C 1

-C

4 -alkyl) The malonates VIII are known from the literature [J. Am. Chem. Soc. 64 (1942), 2714; J. Org. Chem. 39 (1974), 2172; HeIv. Chim. Acta 61 (1978), 1565], or they can be 15 prepared in accordance with the literature cited. The subsequent hydrolysis of the ester IX is carried out under generally customary conditions; depending on the various structural elements, alkaline or acidic hydrolysis of the compounds IX may be advantageous. Under the conditions of the ester 20 hydrolysis, there may be complete or partial decarboxylation, giving I. The decarboxylation is usually carried out at temperatures of from 20 0 C to 180 0 C, preferably from 50 0 C to 120 0 C, in an inert solvent, if appropriate in the presence of an acid. 25 Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid. Suitable solvents are water, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene 30 chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, 8 isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide; particularly preferably, the reaction is carried out in hydrochloric acid or acetic acid. It is also possible to use mixtures of the solvents mentioned. 5 Compounds of the formula I in which X is C 1

-C

4 -alkyl can also be prepared by coupling 5-halotriazolopyrimidines of the formula I in which X is halogen with organometallic reagents of the formula X. In one embodiment of this process, the reaction is carried out with transition metal catalysis, such as Ni or Pd catalysis. 10 I (X = Hal) + MY(-X")y I (X = C 1

-C

4 -alkyl) X In formula X, M is a metal ion of valency y, such as, for example, B, Zn or Sn, and X" is Cl-C 3 -alkyl. This reaction can be carried out, for example, analogously to the following 15 methods: J. Chem. Soc. Perkin Trans. 1 (1994), 1187, ibid. 1 (1996) 2345; WO-A 99/41255; Aust. J. Chem. 43 (1990), 733; J. Org. Chem. 43 (1978), 358; J. Chem. Soc. Chem. Commun. (1979), 866; Tetrahedron Lett. 34 (1993), 8267; ibid. 33 (1992), 413. 20 The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. 25 If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds I cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds I. 30 If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants 35 in the treated plants, or in the harmful fungus to be controlled. In the definitions of the symbols given in the formulae above, collective terms were used which are generally representative of the following substituents: 9 halogen: fluorine, chlorine, bromine and iodine; alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 5 8 carbon atoms, for example C 1

-C

6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethyl propyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl pentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 10 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl and 1-ethyl-2-methylpropyl; haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may 15 be replaced by halogen atoms as mentioned above; in particular, C 1

-C

2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 20 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop 2-yl; alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, for example C 2

-C

6 25 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, 1-methyl-2-propenyl, 2-methyl 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 30 1,1-dimethyl-2-propenyl, 1,2-dimethyl-l1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl 1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 35 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl 2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl 2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 40 1-ethyl-1 -butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl- 10 2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1 -methyl-2-propenyl, 1-ethyl-2-methyl-1l-propenyl and 1-ethyl-2-methyl-2-propenyl; haloalkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 5 8 carbon atoms and one or two double bonds in any position (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine; alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon 10 atoms and one or two triple bonds in any position, for example C 2

-C

6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl 15 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl 1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl 3-butynyl, 3,3-dimethyl-1l-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1 -methyl-2-propynyl; 20 cycloalkyl: mono- or bicyclic saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, for example C 3 -CB-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; 25 five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S: - 5- or 6-membered heterocyclyl which contains one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 30 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 35 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl and 2-piperazinyl; 40 - 5-membered heteroaryl which contains one to four nitrogen atoms or one to three 11 nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 5 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl and 1,3,4-triazol-2-yl; - 6-membered heteroaryl which contains one to three or one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain one to 10 three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl; alkylene: divalent unbranched chains of 3 to 5 CH 2 groups, for example CH 2 , CH 2

CH

2 , 15 CH 2

CH

2

CH

2 , CH 2

CH

2

CH

2

CH

2 and CH 2

CH

2

CH

2

CH

2

CH

2 ; oxyalkylene: divalent unbranched chains of 2 to 4 CH 2 groups, where one valency is attached to the skeleton via an oxygen atom, for example OCH 2

CH

2 , OCH 2

CH

2

CH

2 and OCH 2

CH

2

CH

2

CH

2 ; 20 oxyalkyleneoxy: divalent unbranched chains of 1 to 3 CH 2 groups, where both valencies are attached to the skeleton via an oxygen atom, for example OCH 2 0,

OCH

2

CH

2 0 and OCH 2

CH

2

CH

2 0. 25 The scope of the present invention includes the (R)- and (S)-isomers and the racemates of compounds of the formula I having chiral centers. The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of radicals L and R 3 of formula I. 30 With a view to the intended use of the triazolopyrimidines of the formula I, particular preference is given to the following meanings of the substituents, in each case on their own or in combination: 35 Preference is given to compounds of the formula I in which R 1 is not hydrogen. Particular preference is given to compounds I in which R 1 is C 1

-C

6 -alkyl, C 2

-C

6 -alkenyl or Cl-C 8 -haloalkyl. 40 Preference is given to compounds I in which R 1 is a group A: 12 FF F (CH 2 )q-CHR3- A '1 '2 z z in which 5

Z

1 is hydrogen, fluorine or Cl-C 6 -fluoroalkyl,

Z

2 is hydrogen or fluorine, or

Z

1 and Z 2 together form a double bond; q is 0 or 1; and 10 R 3 is hydrogen or methyl. Moreover, preference is given to compounds I in which R 1 is C 3

-C

6 -cycloalkyl which may be substituted by C 1

-C

4 -alkyl. 15 Particular preference is given to compounds I in which R 2 is hydrogen. Preference is likewise given to compounds I in which R 2 is methyl or ethyl. If R 1 and/or R 2 comprise haloalkyl or haloalkenyl groups having a center of chirality, the 20 (S)-isomers are preferred for these groups. In the case of halogen-free alkyl or alkenyl groups having a center of chirality in R' or R 2 , preference is given to the (R)-configured isomers. Preference is furthermore given to compounds I in which R 1 and R 2 together with the 25 nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thiomorpholinyl ring, in particular a piperidinyl ring which, if appropriate, is substituted by one to three groups halogen, C 1

-C

4 -alkyl or Cl-C 4 -haloalkyl. Particular preference is given to the compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a 4-methylpiperidine ring. 30 The invention furthermore preferably provides compounds I in which R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrazole ring which, if appropriate, is substituted by one or two groups halogen, C 1

-C

4 -alkyl or C 1

-C

4 haloalkyl, in particular by 3,5-dimethyl or 3,5-di(trifluoromethyl). 35 In addition, particular preference is also given to compounds of the formula I in which R' is CH(CH 3

)-CH

2

CH

3 , CH(CH 3

)-CH(CH

3

)

2 , CH(CH 3

)-C(CH

3

)

3 , CH(CH 3

)-CF

3 ,

CH

2

C(CH

3

)=CH

2 , CH 2

CH=CH

2 , cyclopentyl or cyclohexyl; R 2 is hydrogen or methyl; or 13

R

1 and R 2 together are -(CH 2

)

2

CH(CH

3

)(CH

2

)

2 -, -(CH 2

)

2

CH(CF

3

)(CH

2

)

2 - or

-(CH

2

)

2 0(CH 2

)

2 -. Preference is given to compounds I in which X is halogen, C 1

-C

4 -alkyl, cyano or C 1

-C

4 5 alkoxy, such as chlorine, methyl, cyano, methoxy or ethoxy, especially chlorine or methyl, in particular chlorine. In formula I, Hal is in particular chlorine or fluorine. 10 Preference is furthermore given to compounds I in which L 1 is C 1

-C

2 -alkoxy, such as methoxy; cyano; halomethyl, such as trifluoromethyl or Cl-C 4 -alkoxycarbonyl, such as methoxycarbonyl. In these compounds, L 2 and L 3 are particularly preferably hydrogen. Preference is likewise given to compounds I in which L 2 is C 1

-C

2 -alkoxy, such as 15 methoxy; cyano; halomethyl, such as trifluoromethyl or C 1

-C

4 -alkoxycarbonyl, such as methoxycarbonyl. In these compounds, L' and L 3 are particularly preferably hydrogen. In addition, preference is given to compounds I in which L 3 is hydrogen. 20 A preferred embodiment of the invention relates to compounds of the formula 1.1: G L 3 -N 2 L

H

3 C _NR 2 L N'N - L2 1.1 -Hal N N X Hal in which 25 G is C 2

-C

6 -alkyl, in particular ethyl, n- and isopropyl, n-, sec-, tert-butyl, and

C

1

-C

4 -alkoxymethyl, in particular ethoxymethyl, or C 3

-C

6 -cycloalkyl, in particular cyclopentyl or cyclohexyl;

R

2 is hydrogen or methyl; and X is chlorine, methyl, cyano, methoxy or ethoxy. 30 A further preferred embodiment of the invention relates to compounds in which R' and

R

2 together with the nitrogen atom to which they are attached form a five- or six membered heterocyclyl or heteroaryl which is attached via N and may contain a further heteroatom from the group consisting of O, N and S as ring member and/or may carry 35 one or more substituents from the group consisting of halogen, Cl-C 6 -alkyl, Cl-C 6 -halo- 14 alkyl, C 2

-C

6 -alkenyl, C 2

-C

6 -haloalkenyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C3-C6 alkenyloxy, C 3

-C

6 -haloalkenyloxy, Cl-C 6 -alkylene and oxy-C 1

-C

3 -alkyleneoxy. These compounds correspond in particular to the formula 1.2 33 N I N'N- L 2 1.2 N/NN X Hal 5 NN~X in which D together with the nitrogen atom forms a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain a further heteroatom from the 10 group consisting of O, N and S as ring member and/or may carry one or more substituents from the group consisting of halogen, C 1

-C

4 -alkyl, C 1

-C

4 -alkoxy and

C,-C

2 -haloalkyl; and X is chlorine, methyl, cyano, methoxy or ethoxy. 15 A further preferred embodiment of the invention relates to compounds of the formula 1.3 CF L Y NH L N' \L I.3 N N X Hal in which Y is hydrogen or Cl-C 4 -alkyl, in particular methyl and ethyl, and X is chlorine, 20 methyl, cyano, methoxy or ethoxy. In particular with a view to their use, preference is given to the compounds I compiled in the tables below. Moreover, the groups mentioned for a substituent in the tables are per se, independently of the combination in which they are mentioned, a particularly 25 preferred embodiment of the substituent in question. Table 1 Compounds of the formula I in which X is chlorine, Hal is fluorine, Ll is methoxy, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to 30 one row of Table A 15 Table 2 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is methoxy, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 3 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is methoxy, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 4 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is methoxy, L 2 and L 3 are hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 5 Compounds of the formula I in which X is chlorine, Hal is fluorine, L' is cyano, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 6 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' is cyano, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 7 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is cyano, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 8 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is cyano, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 9 Compounds of the formula I in which X is chlorine, Hal is fluorine, L' is trifluoromethyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 16 Table 10 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is trifluoromethyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 11 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is trifluoromethyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 12 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is trifluoromethyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 13 Compounds of the formula I in which X is chlorine, Hal is fluorine, L l is methoxy carbonyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 14 Compounds of the formula I in which X is cyano, Hal is fluorine, L l is methoxycarbonyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 15 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' is methoxycarbonyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 16 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is methoxy carbonyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 17 Compounds of the formula I in which X is chlorine, Hal is chlorine, L' is methoxy, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 17 Table 18 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 19 Compounds of the formula I in which X is methyl, Hal is chlorine, L ' is methoxy, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 20 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is methoxy, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 21 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is cyano, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 22 Compounds of the formula I in which X is cyano, Hal is chlorine, Ll is cyano, L 2 and L 3 are hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 25 Table 23 Compounds of the formula I in which X is methyl, Hal is chlorine, L l is cyano, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 24 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is cyano, L 2 and

L

3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 25 Compounds of the formula I in which X is chlorine, Hal is chlorine, L 1 is trifluoromethyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 18 Table 26 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is trifluoromethyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 27 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is trifluoromethyl,

L

2 and L 3 are hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 10 Table 28 Compounds of the formula I in which X is methoxy, Hal is chlorine, Ll is trifluoromethyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 29 Compounds of the formula I in which X is chlorine, Hal is chlorine, L l is methoxy carbonyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 30 Compounds of the formula I in which X is cyano, Hal is chlorine, L l is methoxycarbonyl,

L

2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 31 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is methoxy carbonyl, L 2 and L 3 are hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 30 Table 32 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is methoxy carbonyl, L 2 and L 3 are hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 33 Compounds of the formula I in which X is chlorine, Hal is fluorine, L l is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 19 Table 34 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 5 Table 35 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 36 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 37 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 38 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 25 Table 39 Compounds of the formula I in which X is methyl, Hal is fluorine, L' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 40 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 35 Table 41 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 20 Table 42 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 43 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 10 Table 44 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 45 Compounds of the formula I in which X is chlorine, Hal is fluorine, L 1 is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 46 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 47 Compounds of the formula I in which X is methyl, Hal is fluorine, L' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 48 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 49 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 21 Table 50 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 51 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 52 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is hydrogen, L 2 is methoxy, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 53 Compounds of the formula I in which X is chlorine, Hal is chlorine, L l is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 54 Compounds of the formula I in which X is cyano, Hal is chlorine, L ' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 55 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 56 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is hydrogen, L 2 is cyano, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 35 Table 57 Compounds of the formula I in which X is chlorine, Hal is chlorine, L' is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 22 Table 58 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 59 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 60 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is hydrogen, L 2 is trifluoromethyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 61 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 62 Compounds of the formula I in which X is cyano, Hal is chlorine, L' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 63 Compounds of the formula I in which X is methyl, Hal is chlorine, L l is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 64 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is hydrogen, L 2 is methoxycarbonyl, L 3 is hydrogen and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 65 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 23 Table 66 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 67 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 10 Table 68 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 69 Compounds of the formula I in which X is chloro, Hal is fluorine, L l and L 2 are hydrogen, L 3 is chlorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 70 Compounds of the formula I in which X is cyano, Hal is fluorine, L l and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 71 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 72 Compounds of the formula I in which X is methoxy, Hal is fluorine, L' and L 2 are hydrogen, L 3 is chlorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 35 Table 73 Compounds of the formula I in which X is chlorine, Hal is fluorine, L' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 24 Table 74 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 75 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 76 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 77 Compounds of the formula I in which X is chlorine, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 78 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 79 Compounds of the formula I in which X is methyl, Hal is fluorine, L' and L 2 are hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 30 Table 80 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 81 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R' and R 2 corresponds for each compound to one row of Table A 40 25 Table 82 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 83 Compounds of the formula I in which X is methy, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 84 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 85 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 86 Compounds of the formula I in which X is cyano, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 87 Compounds of the formula I in which X is methyl, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 88 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 35 Table 89 Compounds of the formula I in which X is chlorine, Hal is chlorine, L' and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 26 Table 90 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 91 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 92 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 93 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 94 Compounds of the formula I in which X is cyano, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 95 Compounds of the formula I in which X is methyl, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 96 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 97 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' and L 2 are hydrogen, L is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 40 27 Table 98 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 99 Compounds of the formula I in which X is methyl, Hal is chlorine, L' and L 2 are hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 10 Table 100 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 101 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 102 Compounds of the formula I in which X is cyano, Hal is chlorine, L ' and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 103 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 104 Compounds of the formula I in which X is methoxy, Hal is chlorine, L l and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 105 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 40 28 Table 106 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 5 Table 107 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 108 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 109 Compounds of the formula I in which X is chlorine, Hal is fluorine, L l is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 110 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 111 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 30 Table 112 Compounds of the formula I in which X is methoxy, Hal is fluorine, L' is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 113 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 29 Table 114 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 115 Compounds of the formula I in which X is methyl, Hal is fluorine, L' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 116 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 117 Compounds of the formula I in which X is chlorine, Hal is fluorine, L' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 118 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 25 Table 119 Compounds of the formula I in which X is methyl, Hal is fluorine, L' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 120 Compounds of the formula I in which X is methoxy, Hal is fluorine, L' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 35 Table 121 Compounds of the formula I in which X is chlorine, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 30 Table 122 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 123 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 124 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 125 Compounds of the formula I in which X is chlorine, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 126 Compounds of the formula I in which X is cyano, Hal is chlorine, L l is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 127 Compounds of the formula I in which X is methyl, Hal is chlorine, L l is cyano, L 2 iS hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 128 Compounds of the formula I in which X is methoxy, Hal is chlorine, Ll is cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 129 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R' and R 2 corresponds for each compound to one row of Table A 40 31 Table 130 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 131 Compounds of the formula I in which X is methyl, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 132 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 133 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 134 Compounds of the formula I in which X is cyano, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 135 Compounds of the formula I in which X is methyl, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 136 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 137 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 32 Table 138 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 139 Compounds of the formula I in which X is methyl, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 140 Compounds of the formula I in which X is methoxy, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 141 Compounds of the formula I in which X is chlorine, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 142 Compounds of the formula I in which X is cyano, Hal is chlorine, L' is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 143 Compounds of the formula I in which X is methyl, Hal is chlorine, L l is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 144 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is cyano, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 145 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 33 Table 146 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 147 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 148 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 149 Compounds of the formula I in which X is chlorine, Hal is fluorine, L l is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 150 Compounds of the formula I in which X is cyano, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 151 Compounds of the formula I in which X is methyl, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 152 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 153 Compounds of the formula I in which X is chlorine, Hal is fluorine, L l is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R' and R 2 corresponds for each compound to one row of Table A 40 34 Table 154 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 155 Compounds of the formula I in which X is methyl, Hal is fluorine, L' is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 156 Compounds of the formula I in which X is methoxy, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 157 Compounds of the formula I in which X is chlorine, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R' and R 2 corresponds for each compound to one row of Table A 20 Table 158 Compounds of the formula I in which X is cyano, Hal is fluorine, L' is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 159 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 160 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 161 Compounds of the formula I in which X is chlorine, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 35 Table 162 Compounds of the formula I in which X is cyano, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 163 Compounds of the formula I in which X is methyl, Hal is fluorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 164 Compounds of the formula I in which X is methoxy, Hal is fluorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R' and R 2 corresponds for each compound to one row of Table A 15 Table 165 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 166 Compounds of the formula I in which X is cyano, Hal is chlorine, Ll is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 167 Compounds of the formula I in which X is methyl, Hal is chlorine, L , is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 168 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 169 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 36 Table 170 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 171 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 172 Compounds of the formula I in which X is methoxy, Hal is chlorine, L' is methoxy, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 173 Compounds of the formula I in which X is chlorine, Hal is chlorine, L l is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 174 Compounds of the formula I in which X is cyano, Hal is chlorine, L l is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 175 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 176 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 35 Table 177 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 40 37 Table 178 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 5 Table 179 Compounds of the formula I in which X is methyl, Hal is chlorine, Ll is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 10 Table 180 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 15 Table 181 Compounds of the formula I in which X is chlorine, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 20 Table 182 Compounds of the formula I in which X is cyano, Hal is chlorine, L l is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 25 Table 183 Compounds of the formula I in which X is methyl, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 corresponds for each compound to one row of Table A 30 Table 184 Compounds of the formula I in which X is methoxy, Hal is chlorine, L ' is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R' and R 2 corresponds for each compound to one row of Table A 38 Table A No. R A-1 H H A-2 OH 3 H A-3 OH 3

OH

3 A-4 CH 2

OH

3 H A-5 0H 2 0H 3

OH

3 A-6 CH 2 0H 3

OH

2

CH

3 A-7 CH 2

CF

3 H A-8 CH 2 0F 3

OH

3 A-9 0H 2 0F 3

CH

2

CH

3 A-10 CH 2 001 3 H A-1i1 0H1 2 C1 3

OH

3 A-12 0H 2 C1 3 CF1 2 0H 3 A-1 3 CH 2

CH

2 0H 3 H A-14 CH 2

CH

2

OH

3

OH

3 A-15 CH 2

OH

2

OH

3 0H 2 0H 3 A-16 CH 2

OH

2

OH

3

OH

2

OH

2

OH

3 A-.17 CH(OH 3

)

2 H A-18 OH(OH 3

)

2

OH

3 A-19 OH(OH 3

)

2

OH

2

OH

3 A-20 OH 2

OH

2

CH

2

CH

3 H A-21 CH 2

OH

2

OH

2

OH

3

OH

3 A-22 OH 2

OH

2

OH

2

OH

3

OH

2

OH

3 A-23 CH 2

CH

2

CH

2 0H 3

OH

2

CH

2

OH

3 A-24 OH 2

OH

2

OH

2

OH

3

OH

2

OH

2

CH

2

OH

3 A-25 W± OH(0H 3

)-OH

2

OH

3 H A-26 (±CH(0H 3

)-OH

2

OH

3

OH

3 A-27 (±CH(0H 3 )-0H 2 0H 3

OH

2

OH

3 A-28 (S) OH(0H 3 )-0H 2 0H 3 H A-29 (S) OH(0H 3 )-0H 2 0H 3

OH

3 A-30 (S) OH(0H 3 )-0H 2 0H 3 0H 2

CH

3 A-31 (R) OH(0H 3 )-0H 2 0H 3 H A-32 (R) OH(0H 3 )-0H 2 0H 3

OH

3 A-33 (R) OH(0H 3 )-0H 2 0H 3 0H 2 0H 3 A-34 W± OH(0H 3 )-OH(0H 3

)

2 H A-35 (±CH(0H 3 )-OH(0H 3

)

2

OH

3 A-36 (±CH(0H 3 )-OH(0H 3

)

2 0H 2

CH

3 39 No. R R A-37 (S) CH(CH 3

)-CH(CH

3

)

2 H A-38 (S) CH(CH 3

)-CH(CH

3

)

2

OH

3 A-39 (S) CH(CH 3

)-CH(CH

3

)

2

CH

2

CH

3 A-40 (R) CH(CH 3

)-CH(CH

3

)

2 H A-41 (R) CH(CH 3

)-CH(CH

3

)

2

CH

3 A-42 (R) CH(CH 3

)-CH(CH

3

)

2

CH

2

CH

3 A-43 () CH(CH 3

)-C(CH

3

)

3 H A-44 (+) CH(CH 3

)-C(CH

3

)

3

CH

3 A-45 (+) CH(CH 3

)-C(CH

3

)

3

CH

2

CH

3 A-46 (S) CH(CH 3

)-C(CH

3

)

3 H A-47 (S) CH(CH 3

)-C(CH

3

)

3

CH

3 A-48 (S) CH(CH 3

)-C(CH

3

)

3

CH

2

CH

3 A-49 (R) CH(CH 3

)-C(CH

3

)

3 H A-50 (R) CH(CH 3

)-C(CH

3

)

3

CH

3 A-51 (R) CH(CH 3

)-C(CH

3

)

3

CH

2

CH

3 A-52 (+) CH(CH 3

)-CF

3 H A-53 (+) CH(CH 3

)-CF

3

OH

3 A-54 (+) CH(CH 3

)-CF

3

CH

2

CH

3 A-55 (S) CH(CH 3

)-CF

3 H A-56 (S) CH(CH 3

)-CF

3

CH

3 A-57 (S) CH(CH 3

)-CF

3

CH

2

CH

3 A-58 (R) CH(CH 3

)-CF

3 H A-59 (R) CH(CH 3

)-CF

3

CH

3 A-60 (R) CH(CH 3

)-CF

3 CH2CH 3 A-61 (±) CH(CH 3 )-CC1 3 H A-62 () CH(CH 3 )-CC1 3

CH

3 A-63 (±) CH(CH 3 )-CC1 3

CH

2

CH

3 A-64 (S) CH(CH 3 )-CC1 3 H A-65 (S) CH(CH 3 )-CC1 3

CH

3 A-66 (S) CH(CH 3 )-CC1 3 CH2CH 3 A-67 (R) CH(CH 3 )-CC1 3 H A-68 (R) CH(CH 3 )-CC1 3

CH

3 A-69 (R) CH(CH 3 )-CC1 3

CH

2

CH

3 A-70 CH 2

CF

2

CF

3 H A-71 CH 2

CF

2

CF

3

CH

3 A-72 CH 2

CF

2

CF

3

CH

2

CH

3 A-73 CH 2

(CF

2

)

2

CF

3

H

40 No. R A-74 CH 2 (0F 2

)

2 0F 3

OH

3 A-75 CH 2

(CF

2

)

2 0F 3

CH

2

CH

3 A-76 0H 2 0(0H 3 )=0H 2 H A-77 CH 2 0(CH 3 )=0H 2

OH

3 A-78 0H 2 0(CH 3

)=CH

2

CH

2

CH

3 A-79 OH 2 OH=0H 2 H A-80 CH 2 OH=0H 2

OH

3 A-81 OH 2

CH=CH

2

CH

2

CH

3 A-82 OH(0H 3

)OH=CH

2 H A-83 OH(0H 3

)CH=CH

2

OH

3 A-84 CH(CH 3 )CH=0H 2 0H 2 0H 3 A-85 CH(0H 3

)C(OH

3 )=0H 2 H A-86 OH(CH 3

)O(CH,

3

)=CH

2

OH

3 A-87 CH(OH 3

)O(CH

3 )=0H 2

OH

2

CH

3 A-88 0H 2 -O aCH H A-89 OH 2 -O aCH OH 3 A-90 OH 2 -O =-H OH 2

OH

3 A-91 cyclopentyl H A-92 cyclopentyl OH 3 A-93 cyclopentyl OH 2

OH

3 A-94 cyclohexyl H A-95 cyclohexyl OH 3 A-96 cyclohexyl OH 2

OH

3 A-97 CH 2 -0 6

H

5 H A-98 0H 2 -0 6

H

5

OH

3 A-99 0H 2 -0 6

H

5

CH

2

CH

3 A-1 00 -(0H 2

)

2

CH=OHOH

2 A-i 01 -(CH 2

)

2 0(0H 3

)=OHOH

2 A-1 02 -OH(0H 3 )0H 2

-OH=OHOH

2 A-1 03 -(0H 2

)

2 0H(CH 3 )(0H 2

)

2 A-I 04 -(0H 2

)

3

OHFOH

2 A-1 05 -(0H 2

)

2

OHF(CH

2

)

2 A-106 -CH 2 OHF(0H 2

)

3 A-1 07 -(0H 2

)

2 0H(0F 3 )(0H 2

)

2 A-1 08 (H)0C2 A-109 (H)SC2 A-110 -(OH 2

)

5

-

41 No. R R A-111 -(CH 2

)

4 A-112 -CH 2

CH=CHCH

2 A-113 -CH(CH 3

)(CH

2

)

3 A-114 -CH 2

CH(CH

3

)(CH

2

)

2 A-115 -CH(CH 3

)-(CH

2

)

2

-CH(CH

3

)

A-116 -CH(CH 3

)-(CH

2

)

4 A-117 -CH 2

-CH(CH

3

)-(CH

2

)

3 A-118 -(CH 2

)-CH(CH

3

)-CH

2

-CH(CH

3

)-CH

2 A-119 -CH(CH 2

CH

3

)-(CH

2

)

4 A-120 -(CH 2

)

2

-CHOH-(CH

2

)

2 A-121 -(CH 2

)

6 A-122 -CH(CH 3

)-(CH

2

)

5 A-123 -(CH 2

)

2

-N(CH

3

)-(CH

2

)

2 A-124 -N=CH-CH=CH A-125 -N=C(CH 3

)-CH=C(CH

3

)

A-126 -N=C(CF 3

)-CH=C(CF

3

)

The compounds I are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some 5 are systemically effective and they can be used in plant protection as foliar and soil fungicides. They are particularly important in the control of a multitude of fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, 10 soya, coffee, sugar cane, vines, fruits and ornamental plants, and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants. They are especially suitable for controlling the following plant diseases: 15 * Alternaria species on fruit and vegetables, * Bipolaris and Drechslera species on cereals, rice and lawns, * Blumeria graminis (powdery mildew) on cereals, * Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and grapevines, 20 * Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, * Fusarium and Verticillium species on various plants, * Mycosphaerella species on cereals, bananas and peanuts, 42 * Phytophthora infestans on potatoes and tomatoes, * Plasmopara viticola on grapevines, * Podosphaera leucotricha on apples, * Pseudocercosporella herpotrichoides on wheat and barley, 5 * Pseudoperonospora species on hops and cucumbers, * Puccinia species on cereals, * Pyricularia oryzae on rice, * Rhizoctonia species on cotton, rice and lawns, * Septoria tritici and Stagonospora nodorum on wheat, 10 * Uncinula necator on grapevines, * Ustilago species on cereals and sugar cane, and * Venturia species (scab) on apples and pears. The compounds I are also suitable for controlling harmful fungi, such as Paecilomyces 15 variotii, in the protection of materials (e.g. wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. The compounds I are employed by treating the fungi or the plants, seeds, materials or soil to be protected from fungal attack with a fungicidally effective amount of the active 20 compounds. The application can be carried out both before and after the infection of the materials, plants or seeds by the fungi. The fungicidal compositions generally comprise between 0.1 and 95%, preferably between 0.5 and 90%, by weight of active compound. 25 When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha. In seed treatment, amounts of active compound of 1 to 1000 g/100 kg seed preferably 30 1 to 200 g/100 kg, in particular 5 to 100 g/100 kg are generally used. When used in the protection of materials or stored products, the amount of active compound applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, for example, 0.001 g to 35 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material. The compounds I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The 43 application form depends on the particular purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention. The formulations are prepared in a known manner, for example by extending the active 5 compound with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries which are suitable are essentially: - water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), 10 pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used, - carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates); 15 emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose. Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of 20 lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol 25 and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol 30 esters, lignosulfite waste liquors and methylcellulose. Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, 35 cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water. 40 Powders, materials for spreading and dustable products can be prepared by mixing or 44 concomitantly grinding the active substances with a solid carrier. Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples 5 of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and 10 nutshell meal, cellulose powders and other solid carriers. In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum). 15 The following are examples of formulations: 1. Products for dilution with water A Water-soluble concentrates (SL) 10 parts by weight of a compound according to the invention are dissolved in water or 20 in a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water. B Dispersible concentrates (DC) 20 parts by weight of a compound according to the invention are dissolved in 25 cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. C Emulsifiable concentrates (EC) 15 parts by weight of a compound according to the invention are dissolved in xylene 30 with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Dilution with water gives an emulsion. D Emulsions (EW, EO) 40 parts by weight of a compound according to the invention are dissolved in xylene 35 with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This mixture is introduced into water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. 40 E Suspensions (SC, OD) 45 In an agitated ball mill, 20 parts by weight of a compound according to the invention are comminuted with addition of dispersants, wetters and water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. 5 F Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a compound according to the invention are ground finely with addition of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, 10 fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. G Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor 15 stator mill with addition of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. 2. Products to be applied undiluted 20 H Dustable powders (DP) 5 parts by weight of a compound according to the invention are ground finely and mixed intimately with 95% of finely divided kaolin. This gives a dustable product. I Granules (GR, FG, GG, MG) 25 0.5 part by weight of a compound according to the invention is ground finely and associated with 95.5% carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted. J ULV solutions (UL) 30 10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example xylene. This gives a product to be applied undiluted. The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, 35 powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; the intention is to ensure in each case the finest possible distribution of the active compounds according to the invention. 40 46 Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. 5 Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water. The active compound concentrations in the ready-to-use preparations can be varied 10 within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%. The active compounds may also be used successfully in the ultra-low-volume process (ULV), by which it is possible to apply formulations comprising over 95% by weight of 15 active compound, or even to apply the active compound without additives. Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active compounds, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the agents 20 according to the invention in a weight ratio of 1:10 to 10:1. The compositions according to the invention can, in the use form as fungicides, also be present together with other active compounds, e.g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the 25 compositions comprising them in the application form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained. The following list of fungicides, in conjunction with which the compounds according to 30 the invention can be used, is intended to illustrate the possible combinations but does not limit them: * acylalanines, such as benalaxyl, metalaxyl, ofurace or oxadixyl, * amine derivatives, such as aldimorph, dodine, dodemorph, fenpropimorph, 35 fenpropidin, guazatine, iminoctadine, spiroxamine or tridemorph, * anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinyl, * antibiotics, such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin, * azoles, such as bitertanol, bromoconazole, cyproconazole, difenoconazole, 40 dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquinconazole, 47 flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizole or triticonazole, * dicarboximides, such as iprodione, myclozolin, procymidone or vinclozolin, 5 * dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram or zineb, * heterocyclic compounds, such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, 10 probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole or triforine, * copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride or basic copper sulfate, * nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton or nitrophthal 15 isopropyl, * phenylpyrroles, such as fenpiclonil or fludioxonil, * sulfur, * other fungicides, such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezine, diclocymet, 20 diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, tolclofos-methyl, quintozene or zoxamide, * strobilurins, such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, 25 metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, * sulfenic acid derivatives, such as captafol, captan, dichlofluanid, folpet or tolylfluanid, * cinnamides and analogous compounds, such as dimethomorph, flumetover or flumorph. 30 Synthesis examples With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds 35 obtained in this manner are listed in the table that follows, together with physical data.

48 Example 1: Preparation of 5-chloro-6-(2-fluoro-3-trifluoromethylphenyl) 7-(4-methylpiperidinyl)-1,2,4-triazolo[1,5a]pyrimidine a) Dimethyl 2-(2-fluoro-3-trifluoromethylphenyl)malonate 5 A mixture of 5.1 g (0.03 mol) of potassium dimethylmalonate and 1 g of copper bromide in 40 ml of diethylene glycol dimethyl ether was stirred at 1000 for about 1 hour. 2.43 g (0.01 mol) of 2-fluoro-3-trifluorophenylbromobenzene were then added, and the mixture was stirred at 1000C for about another 3 hours. After addition of a further 3 g of 10 potassium dimethylmalonate, stirring was continued at 110OC for 3 hours. The reaction mixture was then acidified with conc. hydrochloric acid and extracted with methyl t-butyl ether (MTBE). The combined organic phases were dried and freed from the solvent. The residue obtained was taken up in cyclohexane/ethyl acetate mixtures 15 and filtered off through silica gel. The eluate was freed from the solvent, the residue was dried. 2.7 g of the title compound were obtained as residue. 1 H-NMR (CDCl 3 , 6 in ppm): 7.75 (t, 1H); 7.6 (t, 1H); 7.3 (t, 1H); 5.1 (s, 1H); 3.8 (s, 6H). 20 b) 5,7-Dihydroxy-6-(2-fluoro-3-trifluoromethylphenyl)-1,2,4-triazolo[1,5a]pyrimidine A solution of 2.7 g (9.2 mmol) of dimethyl 2-(2-fluoro-3-trifluoromethylphenyl)malonate (from ex. la) and 0.8 g (9.5 mmol) of aminotriazole in 2.1 g of tributylamine was stirred at about 1700C for about 3 hours, with distillative removal of methanol. The reaction 25 mixture was then cooled to about 80-100'C, and 20% strength aqueous sodium hydroxide solution was added. The aqueous phase was extracted with MTBE and acidified with conc. hydrochloric acid. The aqueous phase was extracted with methylene chloride, the aqueous phase was filtered off, the filter residue was dissolved in tetrahydrofuran. The combined organic phases were both dried and freed from the 30 solvents. This gave as residue 2.0 g of the title compound as a beige solid which was used for the next reaction without further purification. c) 5,7-Dichloro-6-(2-fluoro-3-trifluoromethylphenyl)-1,2,4-triazolo[1,5a]pyrimidine 35 A solution of 2.0 g (6.7 mmol) of 5,7-dihydroxy-6-(2-fluoro-3-trifluoromethylphenyl) 1,2,4-triazolo[1,5a]pyrimidine (from example 1 b) in 30 ml of phosphorus oxychloride was stirred at 100C for about 5 hours. The excess phosphorus oxychloride was then distilled off, the residue was taken up in methylene chloride and water and this mixture was neutralized using NaHCO 3 . The phases were then separated and the aqueous 40 phase was extracted with methylene chloride. The combined organic phases were then 49 dried and the solvent was distilled off. Chromatography on silica gel using cyclohexane/ethyl acetate mixtures gave 0.9 g of the title compound. 1 H-NMR (CDCI 3 , 6 in ppm): 8.65 (s, 1H); 8.4 (t, 1H); 7.6 (t, 1H); 7.5 (t, 1H). 5 1 d) 5-Chloro-6-(2-fluoro-3-trifluoromethylphenyl)-7-(4-methylpiperidinyl) 1,2,4-triazolo[1,5a]pyrimidine A solution of 0.25 g (0.7 mmol) of 5,7-dichloro-6-(2-fluoro-3-trifluoromethylphenyl) 10 1,2,4-triazolo[1,5a]pyrimidine (from example lc), 0.106 g (146 pl, 1.05 mmol) of trimethylamine and 0.104 g of 4-methylpiperidine (as a 0.8 M solution in methylene chloride) in 4 ml of methylene chloride was stirred at 350C for 5 hours and at 20-25 0 C for 15 hours. The reaction mixture was extracted with dil. hydrochloric acid and brine. The organic phase was dried and freed from the solvent. 0.156 g of the title compound 15 remained as a pale crystal material of m.p. 166-170C. HPLC/MS: Rt=3.929 min; m/z=414 (M'+H) HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany) 20 Mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TFA)/water + 0.1% TFA (gradient from 5:95 to 95:5 over 5 min), 400C. MS: quadrupole electrospray ionization, 80 V (positive mode) 50 C0 0.

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00 0 000 4 5 6Ad OfN 0 0 00 00 0 00 (l) I J Im Im It I I, c , Q L U m, Io co CO M~ OO V Ic IL = = - -co co 0. oo m 019'co L)o 0 0 Cq u - _, _ LI I) 0 0 L) I I _ _ -o m L) co 3 3 51 ~0 co o~ U- oU) 00 - m~ U') 64 ( ) (ot co C C)U r mco -~zE (D U' CO ( 0O 0M 0 0l 0Y 0 000 0 0 0 0 0 o 0 o0 o 0 0£ z w I CN C4 (N -C I (N4 Il m (Ni (i I (Nl m- COj CO4 m CO) CO) CO co Mc - -Ol f CO) CO m ' C') COM:LL C, T ~ CO C' 0I4~ 04 04 0 0 111 *~~~~ , i0~i o 0 6 L) I CI CI I CI I CI I C? C? C? C I M i I I I I I I 52 -l 0~ C CD CC) co ",I m ~ U) mD wO U) N O CD 0 m t "q-U 0 CC N m~~~~ ~ ~ ~ ~ 0)) to U' DL 066466 = E - - - - - - - -~ N ~ m co c o (n c m 0 00 0 0 0 00 0 co c c n c o co m 0 0 00 00 00 00 II II1 NI CN N N Z: mNO I N N o Ac 00- INA - 0 C Nq NN N Al N 0 I ~ O I 1C ) z _- UUC)0LO0LO0CD oCD 53 *'~~) C.C' CO0)~ v;~ C. 0~ 0D OL C.0ONO0 0 0 0 - ~ Y) L C'J )Gm 00 0 0 0 0 0 0 0 C 0 0 oJ 0 0Q 0 000000000 U-U -U LU -U U LL LU I L L x~~ -oo-o-o-o-oo-o-o-o 4N 0 0I 0 N CN N LA LLUI LL LL M10 () LI 0' 0000m-11'o1c c LL LL LL0 0 . -(, - 0 6 IN zo M M I 54 1- 0 N ( U)[-0 D o r-(

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0 oE = = = =o = o = = =0 - =---- --- =z E II I I 0 a00odo 00000000000 CLN o 0 0 I II II o 0 0 II III o0 000 II II II II 0 0 0 SI I I 0000O 00 0 . -000000000- ozz oo~~~ ol ooo oo ol oo m= - oooooooooo ooo 00 0000 000 0) 0 0 0 0 0. 0. 0. 0. 0 0 , 0 , 0 , 0 , 0 T- 0 0 0 0 X 00000 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 I 000 I memA U- I IN N II Uo o SLL LT I T 0 U 0 (L 0 0 0 L U~o - L - -00000000 00= ,zz orIIIxx II - - or 0U , , ,' L 0 c o 0 To- - I m C4 zN N N N co o I II 58 (o "I )C (0 00LO C') N-_ L ~ ~ ~ ~ ~ ~ ~~~~() c - - oo or- 0 0C 00 0 00MM0c;6( 0 0 00 0 000 m m 0 000000000000000000000 M0 M:000 02 o 0 0 0 0 0 0 0 C50 u C5 C5 CNI5C 5 - 5Z -U-L -L L x ~ ~ ~ ~ 2 I 0 C5C 5 C5C 3C5555C55) 5E I Al I 1 0~'~ uO 0 o 0No ~ & 0~ 1~ o co z ~ ~ ~ ~ ~ ~ ~~~1 'cqIIIIIIII 59 C;o -Y 0~ -(D M 0 C Mmr- LO C)w -O m 0 w N '0 - E r-- N~ 4 0 0 00c c u)' (D 't 0 o (00r o' oN zi Elz 00r 0 0 0 000 U-j x 00 000000000000 m o o co m o m o o I Co m. 00 04 L) C)(N I I~ I CoC mo mco coco 0, m ~ C, cq mI I 0O~A I 0 I, coI m I) 0, In 0 q U- =1,1M cn CO ) C,0 L I ) U) 0 U) L 60 co U) 0) - E - - -t- - - 0400 cm z z ~zzzz -j 0 C (N 0 L) L)0 co 0 o91o I I I I I I I I I I I 61 Examples for the action against harmful fungi The fungicidal action of the compounds of the formula I was demonstrated by the following tests. 5 The active compounds were prepared separately as a stock solution with 25 mg of active compound which was made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of 10 solvent/emulsifier of 99 to 1. The mixture was then made up with water to 100 ml. This stock solution was diluted with the solvent/emulsifier/water mixture described to the concentration of active compound stated below. Use example 1 - Activity against gray mold on bell-pepper leaves caused by Botrytis 15 cinerea, protective application Bell-pepper seedlings of the cultivar "Neusiedler Ideal Elite" were, after 2-3 leaves were well developed, sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. The next day, the treated plants were 20 inoculated with a spore suspension of Botrytis cinerea which contained 1.7 x 106 spores/mi in a 2% strength aqueous biomalt solution. The test plants were then placed in a dark climatized chamber at 22 to 24 0 C and high atmospheric humidity. After 5 days, the extent of the fungal infection on the leaves could be determined visually in %. 25 In this test, the plants which had been treated with 63 ppm of the active compounds 1-3, 1-4, 1-7, 1-13 to 1-16, 1-18 to 1-22,1-24 to 1-26, 1-28,1-30 to 1-32, 1-34, 1-38, 1-40, 1-42, 1-45, 1-47 to 1-49, 1-52, 1-54 to 1-57, 1-88, 1-99, 1-106,1-114, 1-116, 1-121, 1-136,1-137, 1-140, 1 144, 1-149, 1-159, 1-167, 1-172, 1-174, 1-176, 1-179, 1-180, 1-182 to 1-185, 1-190, 1-191, I 30 193, 1-199,1-202, 1-207 to 1-209 or 1-215 showed an infection of not more than 30%, whereas the untreated plants were 85% infected. Use example 2: Activity against early blight of tomato caused by Alternaria solani 35 Leaves of potted plants of the cultivar "Goldene Kbnigin" were sprayed to runoff point with an aqueous suspension having the concentration of active compound stated below. The next day, the leaves were infected with an aqueous spore suspension of Alternaria solani in a 2% biomalt solution having a density of 0.17 x 106 spore/ml. The plants were then placed in a water-vapor-saturated chamber at temperatures between 40 20 and 22°C. After 5 days, the disease on the untreated but infected control plants had developed to such an extent that the infection could be determined visually in %.

62 In this test, the plants which had been treated with 63 ppm of the active compounds 1-14, 1-20, I-22, 1-24, 1-26, 1-28, 1-30, 1-33, 1-34, 1-36, 1-45, 1-47, 1-54, 1-60, 1-61, 1-98, 1-103, 1-105, 1-107, I-114, 1-159, 1-167 or 1-182 showed an infection of not more than 30%, whereas the untreated plants were 90% infected.

Claims (10)

1. A triazolopyrimidine of the formula I L 1 R 2 L 3 N N'-N L2 " . .Hal 5 N N X 5 in which the substituents are as defined below: R1 , R 2 independently of one another are Ci-CB-alkyl, Cl-C 8 -haloalkyl, 10 C 3 -C 8 -Cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C3-C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 2 -C 8 -alkynyl, C2-C8 haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S, 15 R 1 and R 2 together with the nitrogen atom to which they are attached may also form a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain a further heteroatom from the group consisting of O, N and S as ring member and/or may carry one or more 20 substituents from the group consisting of halogen, C 1 -C 6 -alkyl, Cl-C 6 haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Cl-C 6 -alkoxy, C-C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, Cl-C 6 -alkylene and oxy-C 1 -C 3 alkyleneoxy; 25 R 1 and/or R 2 may carry one to four identical or different groups Ra: R a is halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, Cl-C 6 alkylcarbonyl, C 3 -C 6 -cycloalkyl, Cl-C 6 -alkoxy, Cl-C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, Cl-C 6 -alkylamino, di-Cl-C 6 30 alkylamino, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -Cycloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C 3 -C 6 -cyclo alkoxy, C 3 -C 6 -cycloalkenyloxy, C-C 3 -oxyalkyleneoxy, phenyl, naphthyl, a five- to ten-membered saturated, partially unsaturated or 35 aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S, 64 where these aliphatic, alicyclic or aromatic groups for their part may be partially or fully halogenated or may carry one to three groups Rb: Rb is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, 5 aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothio 10 carbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the abovementioned alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms; and/or one to three of the following radicals: 15 cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl-C 1 -C 6 -alkoxy, aryl-C 1 -C 6 -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 20 10 ring members and the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or substituted by alkyl or haloalkyl groups; Hal is halogen; 25 L 1 , L 2 are hydrogen, cyano, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy or C(=O)A, where at least one group L ' or L 2 is not hydrogen; A is hydrogen, hydroxy, Cl-C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 6 -haloalkoxy, 30 Cl-C 8 -alkylamino or di-(Cl-C 8 -alkyl)amino; L 3 is hydrogen, halogen, cyano, nitro, C 1 -C 4 -haloalkyl, CI-C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl; 35 X is halogen, cyano, Cl-C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 haloalkoxy.

2. The compound of the formula I according to claim 1 in which R 1 is not hydrogen. 65

3. A compound of the formula 1.1 G L 3 H3C NR 2 L N- N L 2 1.1 Hal N N X Hal 5 in which G is C2-C 6 -alkyl, C 1 -C 4 -alkoxymethyl or C3-C 6 -cycloalkyl; R 2 is hydrogen or methyl; and X is chlorine, methyl, cyano, methoxy or ethoxy and L' to L 3 and Hal are as defined according to claim 1. 10

4. A compound of the formula 1.2 D L 3 N N'N L 1.2 N N X Hal 15 in which D together with the nitrogen atom forms a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain a further heteroatom from the group consisting of O, N and S as ring member and/or may carry one or more substituents from the group consisting of halogen, C 1 -C 4 -alkyl, 20 Cl-C 4 -alkoxy and C 1 -C 2 -haloalkyl; X is chlorine, methyl, cyano, methoxy or ethoxy and Ll to L 3 and Hal are as defined according to claim 1.

5. A process for preparing the compounds of the formula I according to claim 1 in 25 which X is halogen, cyano, C 1 -C 4 -alkyl, Cl-C 4 -alkoxy or C0 1 -C 2 -haloalkoxy, by reacting 5-aminotriazole of the formula II N-NH N NH 2 30 with phenylmalonates of the formula III, 66 L 1 0 3 RO/ 2L III RO L )/ Hal RO OHal in which R is alkyl, to give dihydroxytriazolopyrimidines of the formula IV, L 3 OH L NN L IV 'N-, -. N ,l.[-al 5 N N OI aI halogenation to give the dihalo compounds of the formula V, L 3 Y V N-N L2 V q . .Nl yHal N N Y Hal 10 in which Y is halogen and reaction of V with amines of the formula VI RK R2,N-H VI 15 to give compounds of the formula I in which X is halogen, if desired, to prepare compounds of the formula I in which X is cyano, Cl-C 4 -alkoxy or C 1 -C 2 -halo alkoxy, reaction of compounds I in which X is halogen with compounds of the formula VII 20 M-X' VII which, depending on the group X' to be introduced, are inorganic cyanides, alkoxides or haloalkoxides and in which M is an ammonium, tetraalkylammonium, alkali metal or alkaline earth metal cation, and, if desired, to prepare compounds 25 of the formula I according to claim 1 in which X is alkyl, by reaction of the compounds of the formula I in which X is halogen with malonates of the formula VIII 67 X" O 0 VIII OR OR in which X" is hydrogen or C 1 -C 3 -alkyl and R is C 1 -C 4 -alkyl, to give compounds of 5 the formula IX L 1 2 L3 R'R L N'N L2 IX N N Hal X"I ROOC COOR and decarboxylation to give compounds I in which X is alkyl. 10

6. A process for preparing the compounds of the formula I according to claim 1 in which X is CI-C 4 -alkyl or Cl-C 4 -haloalkyl by reacting 5-aminotriazole of the formula II according to claim 5 with keto esters of the formula Ila L 3 RO L Ilia 15 X 1 O Hal 15 0 in which X 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and R is C 1 -C 4 -alkyl, to give 5-alkyl

7-hydroxy-6-phenyltriazolopyrimidines of the formula IVa, L 3 OH N- N L 2 IVa "NI,.N X Hal 20 N N halogenation of IVa to give 7-halotriazolopyrimidines of the formula Va 68 L 1 3 N N L2 Va N N X 1 Hal in which Y is halogen and reaction of Va with amines of the formula VI according to claim 5 to give compounds I in which X is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl. 5 7. The compound of the formula IV, IVa, V or Va according to claims 5 and 6.

8. A fungicidal composition, comprising a solid or liquid carrier and a compound of the formula I according to claim 1. 10

9. Seed, comprising 1 to 1000 g of a compound of the formula I according to claim 1 per 100 kg.

10. A method for controlling phytopathogenic harmful fungi, which method comprises 15 treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of a compound of the formula I according to claim 1. 69 6-(2-Halophenyl)-triazolopyrimidines, method for their production and their use for combating pathogenic fungi, in addition to agents comprising said substances Abstract 5 Triazolopyrimidines of the formula I L 1 2 3 R N'R L N- N'N L2 < Hal N N X Hal 10 in which the substituents are as defined below: R 1 , R 2 are hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, cycloalkenyl, halocycloalkenyl, alkynyl, haloalkynyl or phenyl, naphthyl, or a five or six-membered saturated, partially unsaturated or aromatic heterocycle which 15 contains one to four heteroatoms from the group consisting of O, N and S, R 1 and R 2 together with the nitrogen atom to which they are attached may also form a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain a further heteroatom from the group consisting of O, N and S as 20 ring member and may be substituted as defined in the description; L', L 2 are hydrogen, cyano, haloalkyl, alkoxy, alkenyloxy or C(=O)A, where at least one group L ' or L 2 is not hydrogen; 25 A is hydrogen, hydroxyl, alkyl, alkoxy, haloalkoxy, Cl-C 8 -alkylamino or dialkylamino; L 3 is hydrogen, halogen, cyano, nitro, haloalkyl, alkoxy or alkoxycarbonyl; 30 X is halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy; processes and intermediates for preparing these compounds, compositions comprising them and their use for controlling phytopathogenic harmful fungi.